For $5000 and you like the Italian style, you can take the plane, get off in Rome and then come in Macerata, buy with the remaining 1 o 2 pairs of handmade shoes and 3 / 4 casual shoes. As our district are: Silvano Lattanzi, Prada, Tods, Santoni, Lsp Serafini, Piergiacomi, Paciotti, Fabi, Premiata, Bruschi, Hugo Boss etc. Finally, make a nice holiday, "Le Marche" are beautiful!

Assuming the OP is in the U.S., do you mean, if he buys a $1000 ticket to Europe + hotel accomodations so he can buy bespoke from your beloved austro-hungarian friends? In that case, fine, maybe he can get two pairs. We know how much pride you have in your region's bespoke shoes. We get it.